Selective activations

Activating bonds to achieve selective functionalization of complex systems is central to the team’s activities. Our interests in this field are broad and often the fruit of collaborations. We work on methods to activate C(sp²)-Si bonds, on the activation of alkylmagnesium and alkylzinc reagents (C(sp³)–Mg and C(sp³)–Zn) for uses in asymmetric synthesis, on the activation of C–H bonds (ANR CoCaCoLight), and more recently on the activation of N–Si bonds through the implementation of a novel strategy based on aromatic π-acceptor derivatives.

Activation of C–Si bonds

• Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization. Curpanen, S.; Reichert, P.; Lupidi, G.; Poli, G.; Oble, J.; Perez-Luna, A. Beilstein J. Org. Chem. 2022, 18, 1256–1263 ; http://dx.doi.org/10.3762/bjoc.18.131.

• C3−H Silylation of Furfurylimines: Direct Access to a Novel Biobased Versatile Synthetic Platform Derived from Furfural. Curpanen, S.; Poli, G.; Perez-Luna, A.; Oble, J. Asian J. Org. Chem. 2022, 11, e202200199, http://dx.doi.org/10.1002/ajoc.202200199.

Activation de liaisons C–H

• C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis. Kinkutu, G. K.; Louis, C.; Roy, M.; Blanchard, J.; Oble, J. Beilstein J. Org. Chem. 2023, 19, 582–592. doi:10.3762/bjoc.19.43

• A Well-Defined Low-Valent Cobalt Catalyst Co(PMe3)4 with Dimethylzinc: A Simple Catalytic Approach for the Reductive Dimerization of Benzyl Halides. Fallon, B. J.; Corcé, V.; Amatore, M.; Aubert, C.; Chemla, F.; Ferreira, F.; Perez-Luna, A.; Petit, M. New J. Chem. 2016, 40, 9912–9916 ; http://dx.doi.org/10.1039/C6NJ03265F.

• C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the Absence of Reductant. Fallon, B. J.; Derat, E.; Amatore, M.; Aubert, C.; Chemla, F.; Ferreira, F.; Perez-Luna, A.; Petit, M. Org. Lett. 2016, 18, 2292–2295 ; http://dx.doi.org/10.1021/acs.orglett.6b00939.

• C–H Activation/Functionalization Catalyzed by Simple, Well-Defined Low-Valent Cobalt Complexes. Fallon, B. J.; Derat, E.; Amatore, M.; Aubert, C.; Chemla, F.; Ferreira, F.; Perez-Luna, A.; Petit, M. J. Am. Chem. Soc. 2015, 137, 2448–2451 ; http://dx.doi.org/10.1021/ja512728f.

Activation of alkynes

• Catalytic Chemoselective and Stereoselective Semihydrogenation of Alkynes to E-Alkenes Using the Combination of Pd Catalyst and ZnI₂. Maazaoui, R.; Abderrahim, R.; Chemla, F.; Ferreira, F.; Perez-Luna, A.; Jackowski, O. Org. Lett. 2018, 20, 7544–7549 ; http://dx.doi.org/10.1021/acs.orglett.8b03295.

• Conjugated Enyne Synthesis by Rearrangement of Acetylenic Epoxides Mediated by Low-Valence Organotitanium and Organozirconium Reagents. Denichoux, A.; Cyklinsky, M.; Chemla, F.; Ferreira, F.; Pérez-Luna, A. Synlett 2013, 24, 1001–1005 ; http://dx.doi.org/10.1055/s-0032-1316894.

Activation of allylic systems

• Transition-Metal-Free Synthesis of Enantioenriched Tertiary and Quaternary α-Chiral Allylsilanes. Pérez Sevillano, R.; Ferreira, F.; Jackowski, O. Chem. Eur. J. 2023, e202302227; http://dx.doi.org/10.1002/chem.202302227